Elsevier

Tetrahedron Letters

Volume 38, Issue 20, 19 May 1997, Pages 3503-3506
Tetrahedron Letters

Electrophilicities of iminium ions

https://doi.org/10.1016/S0040-4039(97)00675-8Get rights and content

Abstract

Rate constants for the reactions of the iminium ions Me2N+CH2 (1), iPr2N+CH2 (2), Ph(Me)N+CH2 (3), and Me2N+C(Cl)H (4) with nucleophiles were determined by 1H-NMR spectroscopy. By correlation, the electrophilicity parameters E(1) = −7.0, E(2) = −8.0, E(3) = −4.8, and E(4) = −5.8 were obtained, which allow to define scope and limitation of aminomethylations.

Electrophilicity parameters of iminium ions 1–4 were determined that allow to define scope and limitation of electrophilic aminomethylations.

  1. Download : Download full-size image

References (37)

  • M. Tramontini et al.

    Tetrahedron

    (1990)
  • E.F. Kleinman
  • H. Heaney
  • E.F. Kleinman et al.
  • M. Roth et al.

    Angew. Chem.

    (1995)
    M. Roth et al.

    Angew. Chem. Int. Ed. Engl.

    (1995)
  • G. Seybold

    J. Prakt. Chem.

    (1996)
  • A.R. Katritzky et al.

    J. Org. Chem.

    (1993)
  • H. Waldmann

    Synthesis

    (1994)
  • E. Winterfeldt

    J. Prakt. Chem.

    (1994)
  • N. Risch et al.

    Angew. Chem.

    (1994)
    E. Winterfeldt

    Angew. Chem. Int. Ed. Engl.

    (1994)
  • M. Arend et al.

    Angew. Chem.

    (1995)
    M. Arend et al.

    Angew. Chem. Int. Ed. Engl.

    (1995)
  • N. Risch et al.

    Liebigs Ann. Chem.

    (1992)
  • D. Enders et al.

    Angew. Chem.

    (1996)
    D. Enders et al.

    Angew. Chem. Int. Ed. Engl.

    (1996)
  • V. Vinkovic et al.

    Tetrahedron

    (1997)
  • H. Mayr et al.

    Angew. Chem.

    (1994)
    H. Mayr et al.

    Angew. Chem. Int. Ed. Engl.

    (1994)
  • H. Mayr et al.

    Chem. Ber.

    (1994)
  • H. Mayr et al.

    Res. Chem. Intermed.

    (1996)
  • H. Mayr et al.

    Liebigs Ann.

    (1997)
  • Cited by (53)

    • Chapter 9 The electrophilicity index in organic chemistry

      2007, Theoretical and Computational Chemistry
    • Electrophilicity index revisited

      2023, Journal of Computational Chemistry
    • Hydride Shift Mediated C(sp3)─H Bond Functionalization(Internal Redox Reaction)

      2023, Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
    View all citing articles on Scopus
    View full text